Document Detail

Scope and Limitations of 2-Deoxy- and 2,6-Dideoxyglycosyl Bromides as Donors for the Synthesis of β-2-Deoxy- and β-2,6-Dideoxyglycosides.
MedLine Citation:
PMID:  24786757     Owner:  NLM     Status:  Publisher    
It is shown that 2-deoxy- and 2,6-dideoxyglycosyl bromides can be prepared in high yield (72-94%) and engaged in glycosylation reactions with β:α selectivities ≥6:1. Yields of product are 44-90%. Fully armed 2-deoxyglycoside donors are viable, while 2,6-dideoxyglycosides require one electron-withdrawing substituent for high efficiency and β-selectivity. Equatorial C-3 ester protecting groups decrease β-selectivity, and donors bearing an axial C-3 substituent are not suitable. The method is compatible with azide-containing donors and acid-sensitive functional groups.
Miho Kaneko; Seth B Herzon
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2014-5-1
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2014 May 
Date Detail:
Created Date:  2014-5-2     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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